Low temperature redetermination of the structure of [Ni(CO)(η5-C5H5)]2

Evans, C.; Farrugia, L.J.

doi:10.1107/S1600536803012984

Low temperature redetermination of the structure of [Ni(CO)(η⁵-C₅H₅)]₂

The crystal structure of [Ni(CO)(η⁵-C₅H₅)]₂ has been redetermined at 115 K. The low temperature data provide a more precise structure solution and indicate the presence of a minor degree of disorder in the material. There are two molecules in the asymmetric unit.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803012984/bt6287sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803012984/bt6287Isup2.hkl Contains datablock I

CCDC reference: 217388

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Key indicators

Single-crystal X-ray study
T = 115 K
Mean (C-C) = 0.003 Å
R factor = 0.024
wR factor = 0.065
Data-to-parameter ratio = 20.4

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No syntax errors found

ADDSYM reports no extra symmetry

Comment top

The structure of [Ni(CO)(η⁵-C₅H₅)]₂ had been determined previously on two separate occassions, both at room temperature (Byers & Dahl, 1980; Madach et al., 1980). The advances made in crystallographic techniques since this time allowed for a redetermination of the structure at lower temperature with a significant increase in the quality of the structural solution.

As previously reported, there are two independent molecules within the asymmetric unit (Figure 1). The Ni—Ni distances [2.3691 (3) and 2.3575 (3) Å for Ni(1)—Ni(2) and Ni(3)—Ni(4) respectively] are greater than those previously reported [2.3627 (9) and 2.3510 (9) Å Byers & Dahl, 1980; 2.361 (2) and 2.348 (2) Å Madach et al., 1980] though the remaining bond parameters of the molecules display no significant differences. Both molecules possess non-planar Ni₂(CO)₂ units, analogous to that found for Co₂(CO)₈ (Sumner et al., 1964; Leung & Coppens, 1983), with the η⁵-C₅H₅ rings tilted in the opposite direction. The angle between the η⁵-C₅H₅ and NiC₂ planes ranges from 80.3–82.6° across the two molecules.

A minor component of disorder was noted from difference maps and the positions of the nickel atoms in this component identified. Refinement indicated the extent of the disorder to be approximately 1% with the Ni—Ni distances in the minor component [2.32 (2) and 2.34 (2) Å for Ni(1a)—Ni(2a) and Ni(3a)—Ni(4a) respectively] similar to those in the main structure. The positions of the nickel atoms in the minor component of the disorder appear related to those of the major component by a translation of 6.3–6.4 Å along the c axis of the unit cell (Figure 2). The possibility that this electron density was a result of twinning rather than disorder was examined using the ROTAX program (Cooper et al., 2002) to test for the presence of a 2-fold axis though none was identified. Similarly, the set comprising the weakest 655 reflections provided a K-factor of 1.87, lower than generally observed for a genuine twinned structure. There was also no evidence from the diffraction pattern observed for a twinned crystal.

Experimental top

[Ni(CO)(η⁵-C₅H₅)]₂ was obtained from a commercial source. Crystals suitable for structural determination were obtained from a concentrated hexane solution at −20°C. Contrary to previous reports, all crystals obtained through sublimation displayed evidence of twinning and were disregarded.

Computing details top

Data collection: Collect (Nonius BV, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures top

	Fig. 1. View of the two molecules in the asymmetric unit showing the atom-labelling scheme. Ellipsoids are drawn at the 50% probability level with H atoms represented by circles of arbitrary size. The minor component of the disorder has been omitted
	Fig. 2. View of the unit cell indicating the positions of the nickel atoms in both components of the disorder.

(I) top

Crystal data top

C₁₂H₁₀Ni₂O₂	Z = 4
M_r = 303.62	F(000) = 616
Triclinic, P1	D_x = 1.871 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7498 (1) Å	Cell parameters from 133537 reflections
b = 10.8752 (1) Å	θ = 1–35.0°
c = 13.4942 (2) Å	µ = 3.47 mm⁻¹
α = 76.776 (1)°	T = 115 K
β = 81.112 (1)°	Prism, black
γ = 78.449 (1)°	0.40 × 0.28 × 0.15 mm
V = 1077.65 (2) Å³

Data collection top

KappaCCD diffractometer	6276 independent reflections
Radiation source: Enraf Nonius FR590	5839 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
CCD rotation images, thick slices scans	θ_max = 30°, θ_min = 1.6°
Absorption correction: multi-scan (Blessing, 1995)	h = −10→10
T_min = 0.264, T_max = 0.594	k = −15→15
84232 measured reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.025	H-atom parameters constrained
wR(F²) = 0.065	w = 1/[σ²(F_o²) + (0.0315P)² + 0.5418P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
6276 reflections	Δρ_max = 0.62 e Å⁻³
307 parameters	Δρ_min = −0.64 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0030 (4)

Crystal data top

C₁₂H₁₀Ni₂O₂	γ = 78.449 (1)°
M_r = 303.62	V = 1077.65 (2) Å³
Triclinic, P1	Z = 4
a = 7.7498 (1) Å	Mo Kα radiation
b = 10.8752 (1) Å	µ = 3.47 mm⁻¹
c = 13.4942 (2) Å	T = 115 K
α = 76.776 (1)°	0.40 × 0.28 × 0.15 mm
β = 81.112 (1)°

Data collection top

KappaCCD diffractometer	6276 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	5839 reflections with I > 2σ(I)
T_min = 0.264, T_max = 0.594	R_int = 0.071
84232 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.065	H-atom parameters constrained
S = 1.10	Δρ_max = 0.62 e Å⁻³
6276 reflections	Δρ_min = −0.64 e Å⁻³
307 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ni1	0.22846 (2)	0.276719 (17)	0.470339 (13)	0.01510 (5)	0.9893 (6)
Ni2	0.40518 (2)	0.403569 (17)	0.345001 (14)	0.01549 (5)	0.9893 (6)
O1	0.60220 (15)	0.19174 (12)	0.47306 (10)	0.0311 (3)
O2	0.07454 (16)	0.38667 (13)	0.28323 (9)	0.0298 (3)
C1	0.47518 (19)	0.25718 (14)	0.44374 (12)	0.0206 (3)
C2	0.18366 (19)	0.36542 (14)	0.33737 (11)	0.0195 (3)
C11	−0.0354 (2)	0.29308 (17)	0.54332 (12)	0.0263 (3)
H11	−0.1305	0.356	0.5172	0.032*
C12	0.0722 (2)	0.30539 (15)	0.61484 (12)	0.0235 (3)
H12	0.0596	0.3759	0.6474	0.028*
C13	0.2022 (2)	0.19308 (15)	0.62888 (11)	0.0228 (3)
H13	0.2961	0.177	0.6703	0.027*
C14	0.1690 (2)	0.10783 (16)	0.57036 (12)	0.0253 (3)
H14	0.234	0.0244	0.5681	0.03*
C15	0.0229 (2)	0.16948 (18)	0.51673 (13)	0.0286 (3)
H15	−0.0278	0.1356	0.4713	0.034*
C21	0.6220 (2)	0.50014 (17)	0.33382 (14)	0.0298 (4)
H21	0.7019	0.481	0.3842	0.036*
C22	0.4677 (2)	0.59468 (15)	0.32982 (13)	0.0255 (3)
H22	0.4281	0.6529	0.3747	0.031*
C23	0.3834 (2)	0.58662 (15)	0.24689 (12)	0.0241 (3)
H23	0.2734	0.6362	0.2281	0.029*
C24	0.4904 (2)	0.49164 (16)	0.19554 (13)	0.0280 (3)
H24	0.466	0.469	0.1358	0.034*
C25	0.6380 (2)	0.43782 (17)	0.24927 (15)	0.0314 (4)
H25	0.7315	0.3721	0.2326	0.038*
Ni3	0.27696 (2)	0.106655 (17)	0.154043 (14)	0.01574 (5)	0.9893 (6)
Ni4	0.08613 (2)	0.231899 (18)	0.034791 (14)	0.01724 (5)	0.9893 (6)
O3	0.41294 (16)	0.32257 (12)	0.02415 (10)	0.0314 (3)
O4	−0.09044 (16)	0.13918 (14)	0.23367 (10)	0.0365 (3)
C3	0.3095 (2)	0.25505 (14)	0.05641 (11)	0.0203 (3)
C4	0.0303 (2)	0.15367 (15)	0.17137 (12)	0.0230 (3)
C31	0.5362 (2)	−0.00498 (16)	0.14873 (13)	0.0267 (3)
H31	0.6244	0.0058	0.0916	0.032*
C32	0.5029 (2)	0.06396 (16)	0.23048 (15)	0.0322 (4)
H32	0.566	0.1273	0.2377	0.039*
C33	0.3605 (3)	0.02107 (17)	0.29782 (13)	0.0311 (4)
H33	0.3109	0.0493	0.3594	0.037*
C34	0.3030 (2)	−0.07296 (15)	0.25739 (12)	0.0257 (3)
H34	0.2057	−0.1156	0.2861	0.031*
C35	0.4162 (2)	−0.09125 (14)	0.16744 (12)	0.0235 (3)
H35	0.412	−0.1511	0.1268	0.028*
C41	0.0077 (2)	0.38819 (16)	−0.08238 (12)	0.0261 (3)
H41	0.0409	0.4699	−0.0918	0.031*
C42	−0.1419 (2)	0.34940 (19)	−0.02176 (13)	0.0316 (4)
H42	−0.2292	0.3996	0.017	0.038*
C43	−0.1397 (2)	0.2193 (2)	−0.02877 (15)	0.0379 (4)
H43	−0.2236	0.167	0.0067	0.045*
C44	0.0096 (3)	0.18205 (18)	−0.09793 (15)	0.0362 (4)
H44	0.0402	0.1025	−0.1196	0.043*
C45	0.1028 (2)	0.28468 (18)	−0.12799 (12)	0.0282 (3)
H45	0.2114	0.2853	−0.1716	0.034*
Ni1A	0.365 (2)	0.0565 (16)	0.6844 (13)	0.015 (4)*	0.0107 (6)
Ni2A	0.183 (2)	0.174 (2)	0.5624 (15)	0.019 (4)*	0.0107 (6)
Ni3A	0.865 (2)	0.6841 (17)	0.0648 (13)	0.016 (4)*	0.0107 (6)
Ni4A	0.687 (2)	0.5609 (16)	0.1891 (12)	0.014 (4)*	0.0107 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01393 (9)	0.01538 (9)	0.01476 (9)	−0.00276 (6)	−0.00137 (6)	−0.00058 (6)
Ni2	0.01394 (9)	0.01544 (9)	0.01568 (9)	−0.00304 (6)	−0.00117 (6)	−0.00022 (6)
O1	0.0190 (5)	0.0299 (6)	0.0369 (7)	0.0010 (4)	−0.0059 (5)	0.0058 (5)
O2	0.0258 (6)	0.0370 (7)	0.0259 (6)	−0.0102 (5)	−0.0106 (5)	0.0043 (5)
C1	0.0180 (6)	0.0195 (6)	0.0223 (7)	−0.0032 (5)	−0.0015 (5)	−0.0010 (5)
C2	0.0186 (6)	0.0206 (6)	0.0187 (6)	−0.0052 (5)	−0.0021 (5)	−0.0008 (5)
C11	0.0156 (6)	0.0338 (8)	0.0233 (7)	−0.0028 (6)	0.0015 (5)	0.0029 (6)
C12	0.0247 (7)	0.0230 (7)	0.0194 (7)	−0.0018 (6)	0.0032 (5)	−0.0033 (5)
C13	0.0245 (7)	0.0250 (7)	0.0155 (6)	−0.0022 (6)	−0.0020 (5)	0.0006 (5)
C14	0.0308 (8)	0.0178 (7)	0.0232 (7)	−0.0068 (6)	0.0050 (6)	0.0009 (6)
C15	0.0265 (8)	0.0363 (9)	0.0262 (8)	−0.0191 (7)	0.0020 (6)	−0.0042 (7)
C21	0.0231 (7)	0.0316 (8)	0.0332 (8)	−0.0137 (6)	−0.0083 (6)	0.0075 (7)
C22	0.0304 (8)	0.0206 (7)	0.0265 (7)	−0.0106 (6)	0.0002 (6)	−0.0036 (6)
C23	0.0235 (7)	0.0194 (7)	0.0260 (7)	−0.0058 (5)	−0.0039 (6)	0.0046 (6)
C24	0.0355 (8)	0.0274 (8)	0.0201 (7)	−0.0122 (7)	0.0032 (6)	−0.0013 (6)
C25	0.0206 (7)	0.0248 (8)	0.0410 (9)	−0.0043 (6)	0.0110 (7)	−0.0002 (7)
Ni3	0.01522 (9)	0.01507 (9)	0.01543 (9)	−0.00127 (6)	−0.00317 (6)	−0.00030 (6)
Ni4	0.01623 (9)	0.01686 (9)	0.01767 (9)	−0.00220 (7)	−0.00520 (7)	0.00006 (7)
O3	0.0285 (6)	0.0321 (6)	0.0325 (6)	−0.0144 (5)	−0.0092 (5)	0.0075 (5)
O4	0.0211 (6)	0.0423 (7)	0.0340 (7)	−0.0008 (5)	0.0045 (5)	0.0077 (6)
C3	0.0197 (6)	0.0207 (7)	0.0195 (6)	−0.0037 (5)	−0.0054 (5)	0.0002 (5)
C4	0.0195 (6)	0.0216 (7)	0.0243 (7)	−0.0007 (5)	−0.0037 (5)	0.0011 (5)
C31	0.0176 (6)	0.0238 (7)	0.0319 (8)	0.0007 (5)	−0.0011 (6)	0.0031 (6)
C32	0.0315 (8)	0.0234 (8)	0.0444 (10)	−0.0011 (6)	−0.0241 (8)	−0.0026 (7)
C33	0.0433 (10)	0.0270 (8)	0.0185 (7)	0.0100 (7)	−0.0117 (7)	−0.0040 (6)
C34	0.0256 (7)	0.0205 (7)	0.0238 (7)	−0.0005 (6)	−0.0002 (6)	0.0054 (6)
C35	0.0275 (7)	0.0167 (6)	0.0240 (7)	0.0011 (5)	−0.0054 (6)	−0.0025 (5)
C41	0.0340 (8)	0.0224 (7)	0.0211 (7)	−0.0021 (6)	−0.0122 (6)	0.0008 (6)
C42	0.0236 (7)	0.0421 (10)	0.0232 (7)	0.0079 (7)	−0.0084 (6)	−0.0028 (7)
C43	0.0302 (9)	0.0455 (11)	0.0382 (10)	−0.0182 (8)	−0.0198 (8)	0.0115 (8)
C44	0.0477 (11)	0.0265 (8)	0.0407 (10)	0.0003 (7)	−0.0273 (8)	−0.0107 (7)
C45	0.0277 (8)	0.0385 (9)	0.0176 (7)	−0.0006 (7)	−0.0072 (6)	−0.0053 (6)

Geometric parameters (Å, º) top

Ni1—C1	1.8681 (15)	Ni3—C4	1.8696 (15)
Ni1—C2	1.8807 (15)	Ni3—C32	2.0879 (16)
Ni1—C15	2.0956 (15)	Ni3—C33	2.0905 (16)
Ni1—C14	2.1023 (16)	Ni3—C34	2.1176 (15)
Ni1—C13	2.1202 (15)	Ni3—C31	2.1295 (15)
Ni1—C11	2.1205 (15)	Ni3—C35	2.1867 (15)
Ni1—C12	2.1825 (15)	Ni3—Ni4	2.3575 (3)
Ni1—Ni2	2.3691 (3)	Ni4—C4	1.8685 (16)
Ni2—C2	1.8679 (15)	Ni4—C3	1.8733 (15)
Ni2—C1	1.8738 (15)	Ni4—C42	2.0989 (16)
Ni2—C24	2.0925 (16)	Ni4—C41	2.1006 (15)
Ni2—C25	2.0957 (16)	Ni4—C43	2.1049 (17)
Ni2—C23	2.1149 (15)	Ni4—C45	2.1299 (16)
Ni2—C21	2.1224 (16)	Ni4—C44	2.1806 (17)
Ni2—C22	2.1848 (15)	O3—C3	1.1632 (19)
O1—C1	1.1589 (19)	O4—C4	1.1672 (19)
O2—C2	1.1566 (18)	C31—C35	1.406 (2)
C11—C12	1.413 (2)	C31—C32	1.435 (3)
C11—C15	1.438 (3)	C31—H31	0.95
C11—H11	0.95	C32—C33	1.401 (3)
C12—C13	1.416 (2)	C32—H32	0.95
C12—H12	0.95	C33—C34	1.433 (3)
C13—C14	1.429 (2)	C33—H33	0.95
C13—H13	0.95	C34—C35	1.412 (2)
C14—C15	1.408 (2)	C34—H34	0.95
C14—H14	0.95	C35—H35	0.95
C15—H15	0.95	C41—C42	1.391 (2)
C21—C22	1.411 (2)	C41—C45	1.426 (2)
C21—C25	1.433 (3)	C41—H41	0.95
C21—H21	0.95	C42—C43	1.436 (3)
C22—C23	1.407 (2)	C42—H42	0.95
C22—H22	0.95	C43—C44	1.423 (3)
C23—C24	1.429 (2)	C43—H43	0.95
C23—H23	0.95	C44—C45	1.399 (3)
C24—C25	1.404 (3)	C44—H44	0.95
C24—H24	0.95	C45—H45	0.95
C25—H25	0.95	Ni1A—Ni2A	2.32 (2)
Ni3—C3	1.8685 (15)	Ni3A—Ni4A	2.34 (2)

C1—Ni1—C2	95.61 (6)	C3—Ni3—C4	93.72 (7)
C1—Ni1—C15	141.48 (7)	C3—Ni3—C32	103.64 (7)
C2—Ni1—C15	103.16 (7)	C4—Ni3—C32	143.36 (8)
C1—Ni1—C14	107.02 (7)	C3—Ni3—C33	135.63 (7)
C2—Ni1—C14	136.92 (7)	C4—Ni3—C33	108.03 (7)
C15—Ni1—C14	39.19 (7)	C32—Ni3—C33	39.19 (8)
C1—Ni1—C13	100.01 (6)	C3—Ni3—C34	167.00 (6)
C2—Ni1—C13	164.09 (6)	C4—Ni3—C34	99.25 (6)
C15—Ni1—C13	65.90 (7)	C32—Ni3—C34	66.03 (7)
C14—Ni1—C13	39.57 (7)	C33—Ni3—C34	39.82 (7)
C1—Ni1—C11	163.84 (7)	C3—Ni3—C31	102.22 (6)
C2—Ni1—C11	99.15 (6)	C4—Ni3—C31	162.05 (7)
C15—Ni1—C11	39.87 (7)	C32—Ni3—C31	39.76 (7)
C14—Ni1—C11	65.83 (6)	C33—Ni3—C31	65.70 (7)
C13—Ni1—C11	64.98 (6)	C34—Ni3—C31	64.83 (6)
C1—Ni1—C12	125.85 (6)	C3—Ni3—C35	131.30 (6)
C2—Ni1—C12	127.51 (6)	C4—Ni3—C35	124.15 (7)
C15—Ni1—C12	65.49 (7)	C32—Ni3—C35	65.21 (6)
C14—Ni1—C12	65.27 (6)	C33—Ni3—C35	65.16 (6)
C13—Ni1—C12	38.38 (6)	C34—Ni3—C35	38.26 (6)
C11—Ni1—C12	38.31 (6)	C31—Ni3—C35	38.00 (6)
C1—Ni1—Ni2	50.82 (5)	C3—Ni3—Ni4	51.04 (5)
C2—Ni1—Ni2	50.56 (4)	C4—Ni3—Ni4	50.88 (5)
C15—Ni1—Ni2	152.70 (5)	C32—Ni3—Ni4	154.58 (5)
C14—Ni1—Ni2	155.60 (5)	C33—Ni3—Ni4	157.47 (5)
C13—Ni1—Ni2	141.38 (5)	C34—Ni3—Ni4	139.31 (5)
C11—Ni1—Ni2	138.33 (5)	C31—Ni3—Ni4	136.82 (5)
C12—Ni1—Ni2	133.39 (4)	C35—Ni3—Ni4	130.50 (4)
C2—Ni2—C1	95.85 (6)	C4—Ni4—C3	93.59 (7)
C2—Ni2—C24	105.03 (7)	C4—Ni4—C42	109.41 (7)
C1—Ni2—C24	139.17 (7)	C3—Ni4—C42	136.44 (7)
C2—Ni2—C25	139.33 (7)	C4—Ni4—C41	144.21 (7)
C1—Ni2—C25	105.10 (7)	C3—Ni4—C41	104.05 (7)
C24—Ni2—C25	39.17 (7)	C42—Ni4—C41	38.70 (7)
C2—Ni2—C23	99.29 (6)	C4—Ni4—C43	100.68 (7)
C1—Ni2—C23	164.11 (7)	C3—Ni4—C43	165.45 (7)
C24—Ni2—C23	39.69 (7)	C42—Ni4—C43	39.94 (8)
C25—Ni2—C23	65.79 (6)	C41—Ni4—C43	65.51 (7)
C2—Ni2—C21	163.55 (7)	C4—Ni4—C45	163.26 (7)
C1—Ni2—C21	99.77 (7)	C3—Ni4—C45	100.65 (7)
C24—Ni2—C21	65.75 (7)	C42—Ni4—C45	65.50 (7)
C25—Ni2—C21	39.71 (8)	C41—Ni4—C45	39.39 (7)
C23—Ni2—C21	64.75 (6)	C43—Ni4—C45	64.81 (7)
C2—Ni2—C22	126.19 (6)	C4—Ni4—C44	125.46 (8)
C1—Ni2—C22	126.88 (7)	C3—Ni4—C44	128.61 (8)
C24—Ni2—C22	65.23 (6)	C42—Ni4—C44	65.57 (7)
C25—Ni2—C22	65.29 (7)	C41—Ni4—C44	64.83 (7)
C23—Ni2—C22	38.16 (6)	C43—Ni4—C44	38.74 (8)
C21—Ni2—C22	38.22 (7)	C45—Ni4—C44	37.85 (7)
C2—Ni2—Ni1	51.04 (4)	C4—Ni4—Ni3	50.92 (5)
C1—Ni2—Ni1	50.61 (5)	C3—Ni4—Ni3	50.86 (5)
C24—Ni2—Ni1	154.52 (5)	C42—Ni4—Ni3	159.27 (5)
C25—Ni2—Ni1	154.30 (5)	C41—Ni4—Ni3	154.88 (5)
C23—Ni2—Ni1	139.85 (4)	C43—Ni4—Ni3	139.25 (5)
C21—Ni2—Ni1	139.65 (5)	C45—Ni4—Ni3	135.24 (5)
C22—Ni2—Ni1	133.18 (4)	C44—Ni4—Ni3	128.75 (5)
O1—C1—Ni1	140.83 (13)	O3—C3—Ni3	141.24 (13)
O1—C1—Ni2	140.60 (13)	O3—C3—Ni4	140.61 (12)
Ni1—C1—Ni2	78.56 (6)	Ni3—C3—Ni4	78.11 (6)
O2—C2—Ni2	141.60 (12)	O4—C4—Ni4	141.57 (13)
O2—C2—Ni1	139.97 (12)	O4—C4—Ni3	140.22 (13)
Ni2—C2—Ni1	78.39 (6)	Ni4—C4—Ni3	78.20 (6)
C12—C11—C15	108.60 (14)	C35—C31—C32	108.43 (15)
C12—C11—Ni1	73.22 (9)	C35—C31—Ni3	73.20 (9)
C15—C11—Ni1	69.13 (9)	C32—C31—Ni3	68.56 (9)
C12—C11—H11	125.7	C35—C31—H31	125.8
C15—C11—H11	125.7	C32—C31—H31	125.8
Ni1—C11—H11	123.5	Ni3—C31—H31	124
C11—C12—C13	107.27 (14)	C33—C32—C31	107.66 (15)
C11—C12—Ni1	68.47 (9)	C33—C32—Ni3	70.51 (10)
C13—C12—Ni1	68.43 (8)	C31—C32—Ni3	71.68 (9)
C11—C12—H12	126.4	C33—C32—H32	126.2
C13—C12—H12	126.4	C31—C32—H32	126.2
Ni1—C12—H12	128.3	Ni3—C32—H32	123.3
C12—C13—C14	108.70 (14)	C32—C33—C34	107.87 (15)
C12—C13—Ni1	73.19 (9)	C32—C33—Ni3	70.30 (9)
C14—C13—Ni1	69.54 (9)	C34—C33—Ni3	71.11 (9)
C12—C13—H13	125.6	C32—C33—H33	126.1
C14—C13—H13	125.6	C34—C33—H33	126.1
Ni1—C13—H13	123.2	Ni3—C33—H33	124.1
C15—C14—C13	107.84 (15)	C35—C34—C33	108.18 (15)
C15—C14—Ni1	70.15 (9)	C35—C34—Ni3	73.52 (9)
C13—C14—Ni1	70.89 (9)	C33—C34—Ni3	69.07 (9)
C15—C14—H14	126.1	C35—C34—H34	125.9
C13—C14—H14	126.1	C33—C34—H34	125.9
Ni1—C14—H14	124.5	Ni3—C34—H34	123.1
C14—C15—C11	107.49 (15)	C31—C35—C34	107.76 (15)
C14—C15—Ni1	70.66 (9)	C31—C35—Ni3	68.80 (9)
C11—C15—Ni1	70.99 (9)	C34—C35—Ni3	68.22 (8)
C14—C15—H15	126.3	C31—C35—H35	126.1
C11—C15—H15	126.3	C34—C35—H35	126.1
Ni1—C15—H15	123.7	Ni3—C35—H35	128.4
C22—C21—C25	108.63 (15)	C42—C41—C45	108.57 (16)
C22—C21—Ni2	73.28 (9)	C42—C41—Ni4	70.58 (9)
C25—C21—Ni2	69.14 (9)	C45—C41—Ni4	71.41 (9)
C22—C21—H21	125.7	C42—C41—H41	125.7
C25—C21—H21	125.7	C45—C41—H41	125.7
Ni2—C21—H21	123.5	Ni4—C41—H41	123.9
C23—C22—C21	107.22 (15)	C41—C42—C43	107.17 (16)
C23—C22—Ni2	68.23 (9)	C41—C42—Ni4	70.72 (9)
C21—C22—Ni2	68.49 (9)	C43—C42—Ni4	70.26 (10)
C23—C22—H22	126.4	C41—C42—H42	126.4
C21—C22—H22	126.4	C43—C42—H42	126.4
Ni2—C22—H22	128.4	Ni4—C42—H42	124.2
C22—C23—C24	108.87 (14)	C44—C43—C42	108.37 (16)
C22—C23—Ni2	73.61 (9)	C44—C43—Ni4	73.50 (10)
C24—C23—Ni2	69.31 (9)	C42—C43—Ni4	69.80 (10)
C22—C23—H23	125.6	C44—C43—H43	125.8
C24—C23—H23	125.6	C42—C43—H43	125.8
Ni2—C23—H23	123.1	Ni4—C43—H43	122.5
C25—C24—C23	107.67 (15)	C45—C44—C43	107.07 (16)
C25—C24—Ni2	70.53 (9)	C45—C44—Ni4	69.11 (9)
C23—C24—Ni2	71.00 (9)	C43—C44—Ni4	67.76 (10)
C25—C24—H24	126.2	C45—C44—H44	126.5
C23—C24—H24	126.2	C43—C44—H44	126.5
Ni2—C24—H24	123.9	Ni4—C44—H44	128.2
C24—C25—C21	107.52 (15)	C44—C45—C41	108.71 (16)
C24—C25—Ni2	70.29 (9)	C44—C45—Ni4	73.04 (10)
C21—C25—Ni2	71.15 (9)	C41—C45—Ni4	69.19 (9)
C24—C25—H25	126.2	C44—C45—H45	125.6
C21—C25—H25	126.2	C41—C45—H45	125.6
Ni2—C25—H25	123.9	Ni4—C45—H45	123.7

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀Ni₂O₂
M_r	303.62
Crystal system, space group	Triclinic, P1
Temperature (K)	115
a, b, c (Å)	7.7498 (1), 10.8752 (1), 13.4942 (2)
α, β, γ (°)	76.776 (1), 81.112 (1), 78.449 (1)
V (Å³)	1077.65 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.47
Crystal size (mm)	0.40 × 0.28 × 0.15

Data collection
Diffractometer	KappaCCD diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.264, 0.594
No. of measured, independent and observed [I > 2σ(I)] reflections	84232, 6276, 5839
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.065, 1.10
No. of reflections	6276
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.64

Computer programs: Collect (Nonius BV, 1997-2000), HKL SCALEPACK (Otwinowski & Minor 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX publication routines (Farrugia, 1999).

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